I am a serial entrepreneur and professor turned venture capitalist. I led Computer Motion’s $110 million IPO and the $236 million sale of Expertcity (creator of GoToMyPC and GoToMeeting) to Citrix. I also contributed to CallWave’s IPO, sold a company I Co-founded to Coull and managed The Tearaways, a gifted power pop band. At Rincon Venture Partners, I am honored to work with some of the most talented startup operators on the planet.

“One of the big misconceptions in baseball is that playing the game keeps you in shape to pitch. I wish that was true. It’s not.” Steven Ellis, Professional Pitcher

Major League baseball pitchers spend far more time preparing to pitch than they actually do pitching. The same should be true of an entrepreneur who is attempting to secure money from sophisticated investors.

The steps outlined below represent an ideal approach to raising capital from sophisticated investors. Unfortunately, your fundraising efforts will be less linear. You might be at Step 2 with one VC and Step 3 with another. However, the greater degree that you can sequentially follow these steps while keeping your discussions with each venture capitalist (VC) at relatively the same stage, the sooner you can spend less time in the company of investors and get back to running your business.

Prep Steps

Step 1: The Person, Not The Firm – As Brad Feld and Jason Mendelson make clear in their book Venture Deals, entrepreneurs should identify specific venture partners, rather than target firms as a whole. Partners can differ greatly at the same firm, with respect to operational experiences, proclivities, temperament and capabilities.

One way to accelerate your research is to speak with other startup CEOs who recently closed fundraising rounds. They can provide insights into which firms are moving aggressively, which are nearly out of money, which partners are douches, etc.

Don Charlton, Founder and CEO of The Resumator (a Rincon portfolio company), recently took this approach. According to Don, “Even though we had high-profile clients such as Tumblr, Pintrest, Klout, Bit.ly, Mashable and Evernote, I knew that raising our B round was going to be time consuming. By comparing notes with a couple of other CEOs who were also raising money, I was able to short circuit a number of potentially dead-end meetings. VCs frequently collude, it’s only fair that entrepreneurs compare notes every now and again as well.”

Step 2: Get Personal & Give Freely – Once you identify a handful of potential VC partners, stealthily cyber stalk them. Follow them on Twitter, Quora and become familiar with their Facebook presence. Subscribe to their blog. Send them a private message via Twitter or Quora that contains a compelling link relevant to their investment focus. Judiciously comment on articles they post to LinkedIn, retweet their tweets, vote up some of their Quora posts and establish a Google Alert on them and their firm.

Based on your research from Step 1, you should be able to communicate meaningful and insightful comments related to the partners’ online presence. Even the most jaded VC cannot resist authentic flattery. The keyword here is authentic. Thoughtfully done in moderation, consistently over an extended period, these small, supportive gestures will not go unnoticed or unappreciated. Done excessively, you risk being labeled a clueless amateur.

Once you establish a modest level of the partner’s cyber-attention, determine how you can help them. For instance, assuming your target VC has a portfolio of investments somewhat related to your business, it is likely that some of your partners, vendors and other stakeholders will be applicable to a subset of the investor’s portfolio. If this is the case, offer to make a meaningful introduction to a potential customer or partner of one of their portfolio companies. If the investor connects you with one of his portfolio CEOs, it will facilitate completion of Step 3.

Step 3: Meaningful Referral – Fundraising books often instruct entrepreneurs to seek referrals to a VC from accountants and lawyers. While these referrals are not completely worthless, they are far from ideal. Professional service providers are incentivized to foster your business, as a portion of the funds you raise will go toward payment of their invoices.

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